6-Bromo-5-methoxy-2h-3,1-benzoxazine-2,4(1h)-dione → Methyl 6-amino-3-bromo-2-methoxybenzoate

HRID 1726014Notes

Reaction equation

HRID 1726014 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=O)[O:8][C:7](=[O:12])[C:6]=2[C:13]=1[O:14][CH3:15]>CO>[NH2:10][C:5]1[C:6]([C:7]([O:8][CH3:9])=[O:12])=[C:13]([O:14][CH3:15])[C:2]([Br:1])=[CH:3][CH:4]=1

Participants

3

Reactant 1

HCID 876056556-Bromo-5-methoxy-2h-3,1-benzoxazine-2,4(1h)-dione

Product 1

HCID 68866280Methyl 6-amino-3-bromo-2-methoxybenzoateYield 87.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 385B (6.83 g, 25.2 mmol) in anhydrous methanol (300 mL) was refluxed for 48 hours. The solution was concentrated and the residue was purified by chromatography on a silica gel column eluting with 20% ethyl acetate/hexane to give the desired product 5.7 g, 87.2% yield. 1H NMR (DMSO-d6) δ 3.70 (s, 3H), 3.82 (s, 3H), 5.92 (s, 2H), 6.45 (d, 1H), 7.30 (d, 1H); MS (ESI(−)) m/e 258, 260 (M−H)−.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by chromatography on a silica gel column
  3. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b3f9a847930b4bf19cee5f42f2594e3a
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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